| Super League | 21/01/18 | Olympiakos Piraeus | - | Xanthi FC | 3:0 | ||||
| Super League | 09/12/18 | Xanthi FC | - | Olympiakos Piraeus | 1:1 |  |
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| Kypello | 08/01/19 | Xanthi FC | - | Olympiakos Piraeus | 0:0 | ||||
| Kypello | 23/01/19 | Olympiakos Piraeus | - | Xanthi FC | 3:1 | ||||
| Super League | 02/11/19 | Xanthi FC | - | Olympiakos Piraeus | 0:0 | ||||
| Super League | 01/02/20 | Olympiakos Piraeus | - | Xanthi FC | 3:1 |
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